This invention relates to the preparation of a tetra- or pentahalophenylvinylbenzyl ether from the reaction of the corresponding halophenoxide with a vinylbenzyl chloride in an organic solvent.
U.S. Pat. No. 3,058,953 discloses that halo-phenylvinylbenzyl ethers can be prepared by the reaction of a halophenol with a vinylbenzyl chloride in the presence of aqueous alkali or alkaline earth hydroxide and a polymerization inhibitor in a liquid solvent. The solvent must be a highly polar one such as dioxane or dimethylformamide in admixture with water. This method of preparing a halophenylvinylbenzyl ether suffers from numerous deficiencies which have limited its utility. First, this method utilizes high boiling solvents, such as dioxane and dimethylformamide, which are difficult to remove from the precipitated product of the reaction. Second, the presence of excess hydroxide ions can hydrolyze vinylbenzyl chloride to vinylbenzyl alcohol. The vinylbenzyl alcohol in turn reacts with vinylbenzyl chloride to produce vinylbenzyl ether, an undesirable cross-linking compound in any subsequent vinyl polymerization of the product.
In view of the aforementioned deficiencies in the prior art method, it would be highly desirable to provide a method of preparing halophenylvinylbenzyl ether free of such contaminants.